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  4. Which one of the following can not be made from 1-bromopropane in a single step?

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Q. Which one of the following can not be made from 1-bromopropane in a single step?

AMUAMU 2013

Solution:

Propane can be made from $1$-bromopropane in a single step by reduction.
$LiAlH _{4}+4 CH _{3} CH _{2} CH _{2} Br \rightarrow$
$4 CH _{3} CH _{2} CH _{3}+ AlBr _{3}+ LiBr LiAlH _{4}$
is a hydride donoar ( $H ^{-}$donor).
Note $3^{\circ}$ alkyl halides give alkenes.
Because they undergo dehydrohalogenation.
$CH _{3} CH _{2} CH _{2} Br \xrightarrow[\Delta]{\text { Alcoholic } KOH }$
$CH _{3} CH = CH _{2}+ KCl + H _{2} O$ (elimination)
$CH_3CH_2CH_2Br \xrightarrow[37.3\,K]{aq. KOH} $
$CH_3CH_2CH_2OH + KBr$ (sublimation)
$CH_3CH_2CH_2Br \xrightarrow[\text{in presence of} C_2H_5OH]{H - NH_2, \Delta}$
$ CH_3CH_2CH_2NH_2$ (Substitution)